9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine

Base Information

• Chemical Name: 9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine
• CAS No.: 873556-44-6
• Molecular Formula: C18H24N8O5
• Molecular Weight: 432.439
• DSSTox Substance ID: DTXSID00705003
• Mol file: 873556-44-6.mol

Synonyms:DTXSID00705003;9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine

Chemical Property of 9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine

Chemical Property:

• PSA: 162.86000
• LogP: 2.36746
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 432.18696590
• Heavy Atom Count: 31
• Complexity: 739

Purity/Quality:

95% ^*data from raw suppliers

5'-Azido-N6-Boc-5'-deoxy-2',3'-O-isopropylideneadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=NC4=C(N=CN=C43)NC(=O)OC(C)(C)C)CN=[N+]=[N-])C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H](O[C@@H](C2O1)CN=[N+]=[N-])N3C=NC4=C(N=CN=C43)NC(=O)OC(C)(C)C)C

Technology Process of 9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine

There total 6 articles about 9-[(3xi)-5-Azido-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-threo-pentofuranosyl]-N-(tert-butoxycarbonyl)-9H-purin-6-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

tert-butyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (686301-05-3) → tert-butyl (9-((3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (873556-44-6)

Guidance literature:

tert-butyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.166667h;

With diphenylphosphoranyl azide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2008.07.130

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2) → tert-butyl (9-((3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (873556-44-6)

Guidance literature:

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → tert-butyl (9-((3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (873556-44-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole / CH₂Cl₂ / 16 h

2.1: NaH / tetrahydrofuran; dimethylformamide / 0 °C

2.2: 5.5 g / tetrahydrofuran; dimethylformamide / 16 h

3.1: 100 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

4.1: 48 percent / PPh₃; CBr₄; NaN₃ / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; sodium azide; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm051060o

upstream raw materials:

tert-butyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

di-tert-butyl dicarbonate

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine

tert-butyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

Downstream raw materials:

N⁶-tert-butoxycarbonyl-5'-N-(4-(2-benzyloxybenzoyl)-1H-1,2,3-triazol-1-yl)-5'-deoxy-2',3'-O-isopropylideneadenosine

tert-butyl 9-(((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate

(E)-5'-deoxy-5'-N-({[2-(2-hydroxyphenyl)ethenyl]sulfonyl}amino)adenosine

(E)-5'-deoxy-5'-N-({2-[2-(methoxymethoxy)phenyl]ethenyl}sulfonyl)amino-2',3'-O-isopropylideneadenosine